EA001313B1 - Пестициды - Google Patents
Пестициды Download PDFInfo
- Publication number
- EA001313B1 EA001313B1 EA199800507A EA199800507A EA001313B1 EA 001313 B1 EA001313 B1 EA 001313B1 EA 199800507 A EA199800507 A EA 199800507A EA 199800507 A EA199800507 A EA 199800507A EA 001313 B1 EA001313 B1 EA 001313B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- halogen
- group
- haloidc1
- c6alkyl
- Prior art date
Links
- 239000000575 pesticide Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 676
- 125000001424 substituent group Chemical group 0.000 claims abstract description 314
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 226
- -1 haloidC1-C4alkyl Chemical group 0.000 claims abstract description 157
- 150000002367 halogens Chemical class 0.000 claims abstract description 153
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 99
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 89
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 80
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 79
- 125000003118 aryl group Chemical group 0.000 claims abstract description 42
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 23
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 22
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 19
- 239000000460 chlorine Chemical group 0.000 claims abstract description 18
- 229910052801 chlorine Chemical group 0.000 claims abstract description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 18
- 239000011737 fluorine Substances 0.000 claims abstract description 17
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 17
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims abstract description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 12
- 238000006467 substitution reaction Methods 0.000 claims abstract description 12
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 9
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 9
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 8
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 7
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 7
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 5
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003963 dichloro group Chemical group Cl* 0.000 claims abstract description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000000203 mixture Substances 0.000 claims description 83
- 239000013543 active substance Substances 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 50
- 229910052799 carbon Inorganic materials 0.000 claims description 47
- 230000000694 effects Effects 0.000 claims description 37
- 150000003839 salts Chemical group 0.000 claims description 37
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
- 239000013256 coordination polymer Substances 0.000 claims description 18
- 241000607479 Yersinia pestis Species 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 229910052700 potassium Inorganic materials 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 230000008520 organization Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 abstract 2
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 abstract 1
- 101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 99
- 229920005989 resin Polymers 0.000 description 99
- 241000196324 Embryophyta Species 0.000 description 71
- 239000003921 oil Substances 0.000 description 66
- 235000019198 oils Nutrition 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- 150000003254 radicals Chemical class 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 22
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 241000233866 Fungi Species 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
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- 240000007594 Oryza sativa Species 0.000 description 13
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 13
- 229940049953 phenylacetate Drugs 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 12
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 10
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- 239000007864 aqueous solution Substances 0.000 description 9
- 125000001246 bromo group Chemical group Br* 0.000 description 9
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- VZWXKHOUNIHGII-UHFFFAOYSA-N 1-[4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]propane-1,2-dione Chemical compound C1=CC(C(=O)C(=O)C)=CC=C1OCC1=CC=CC(C(F)(F)F)=C1 VZWXKHOUNIHGII-UHFFFAOYSA-N 0.000 description 7
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- 239000013067 intermediate product Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- QWKORJYDIOUMQD-UHFFFAOYSA-N methyl 2-[2-[[[1-(2-fluoro-4-methoxyphenyl)-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-2-methoxyiminoacetate Chemical compound C=1C=C(OC)C=C(F)C=1C(=NOC)C(C)=NOCC1=CC=CC=C1C(=NOC)C(=O)OC QWKORJYDIOUMQD-UHFFFAOYSA-N 0.000 description 1
- PODAVBVROVMMPS-UHFFFAOYSA-N methyl 2-[2-[[[1-(2-fluoro-4-methylphenyl)-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-2-methoxyiminoacetate Chemical compound C=1C=C(C)C=C(F)C=1C(=NOC)C(C)=NOCC1=CC=CC=C1C(=NOC)C(=O)OC PODAVBVROVMMPS-UHFFFAOYSA-N 0.000 description 1
- JSBMXWJQFLEDMU-UHFFFAOYSA-N methyl 2-[2-[[[1-(2-fluoro-4-propoxyphenyl)-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-2-methoxyiminoacetate Chemical compound FC1=CC(OCCC)=CC=C1C(=NOC)C(C)=NOCC1=CC=CC=C1C(=NOC)C(=O)OC JSBMXWJQFLEDMU-UHFFFAOYSA-N 0.000 description 1
- KLJSMAUKTFFXQS-UHFFFAOYSA-N methyl 2-[2-[[[1-(4-cyclopentyloxyphenyl)-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-2-methoxyiminoacetate Chemical compound C=1C=C(OC2CCCC2)C=CC=1C(=NOC)C(C)=NOCC1=CC=CC=C1C(=NOC)C(=O)OC KLJSMAUKTFFXQS-UHFFFAOYSA-N 0.000 description 1
- SDOJTOLWSZQAMA-UHFFFAOYSA-N methyl 2-[2-[[[1-(4-ethoxy-2-fluorophenyl)-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-2-methoxyiminoacetate Chemical compound FC1=CC(OCC)=CC=C1C(=NOC)C(C)=NOCC1=CC=CC=C1C(=NOC)C(=O)OC SDOJTOLWSZQAMA-UHFFFAOYSA-N 0.000 description 1
- DSQAXDVLRQUWAF-UHFFFAOYSA-N methyl 2-[2-[[[1-(4-fluoro-2-methylphenyl)-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-2-methoxyiminoacetate Chemical compound C=1C=C(F)C=C(C)C=1C(=NOC)C(C)=NOCC1=CC=CC=C1C(=NOC)C(=O)OC DSQAXDVLRQUWAF-UHFFFAOYSA-N 0.000 description 1
- CZRMDXFWSIKMGC-UHFFFAOYSA-N methyl 2-[2-[[[1-[2,5-difluoro-4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C(C(=C1)F)=CC(F)=C1OCC1=CC=CC(C(F)(F)F)=C1 CZRMDXFWSIKMGC-UHFFFAOYSA-N 0.000 description 1
- QSYFGYJJCPLPPH-UHFFFAOYSA-N methyl 2-[2-[[[1-[2-fluoro-4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C(C(=C1)F)=CC=C1OCC1=CC=CC(C(F)(F)F)=C1 QSYFGYJJCPLPPH-UHFFFAOYSA-N 0.000 description 1
- FXUIPCSYKZIMDM-UHFFFAOYSA-N methyl 2-[2-[[[1-[3,5-difluoro-4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C(C=C1F)=CC(F)=C1OCC1=CC=CC(C(F)(F)F)=C1 FXUIPCSYKZIMDM-UHFFFAOYSA-N 0.000 description 1
- VXZBRODDSGHALE-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-(3,4-dichlorophenoxy)phenyl]-1-ethoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound C=1C=C(OC=2C=C(Cl)C(Cl)=CC=2)C=CC=1C(=NOCC)C(C)=NOCC1=CC=CC=C1C(=COC)C(=O)OC VXZBRODDSGHALE-UHFFFAOYSA-N 0.000 description 1
- FRTUITDNARBPTB-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-(3-chlorophenoxy)phenyl]-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C(C=C1)=CC=C1OC1=CC=CC(Cl)=C1 FRTUITDNARBPTB-UHFFFAOYSA-N 0.000 description 1
- UQMMMUKXRVCHSG-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-(4-bromophenoxy)phenyl]-1-ethoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound C=1C=C(OC=2C=CC(Br)=CC=2)C=CC=1C(=NOCC)C(C)=NOCC1=CC=CC=C1C(=COC)C(=O)OC UQMMMUKXRVCHSG-UHFFFAOYSA-N 0.000 description 1
- POMDOXSFXXYJPO-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-(4-bromophenoxy)phenyl]-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C(C=C1)=CC=C1OC1=CC=C(Br)C=C1 POMDOXSFXXYJPO-UHFFFAOYSA-N 0.000 description 1
- FRNDRHFABNSWED-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-(4-chlorophenoxy)phenyl]-1-ethoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1C(=NOCC)C(C)=NOCC1=CC=CC=C1C(=COC)C(=O)OC FRNDRHFABNSWED-UHFFFAOYSA-N 0.000 description 1
- VRTOOPACWOQOGP-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-(4-tert-butylphenoxy)phenyl]-1-ethoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound C=1C=C(OC=2C=CC(=CC=2)C(C)(C)C)C=CC=1C(=NOCC)C(C)=NOCC1=CC=CC=C1C(=COC)C(=O)OC VRTOOPACWOQOGP-UHFFFAOYSA-N 0.000 description 1
- WICDBMOZHBWVRD-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-[(2,2-dichlorocyclopropyl)methoxy]-2,5-difluorophenyl]-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C(C(=C1)F)=CC(F)=C1OCC1C(Cl)(Cl)C1 WICDBMOZHBWVRD-UHFFFAOYSA-N 0.000 description 1
- SUKKLVJALGDLLT-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-[(2,2-dichlorocyclopropyl)methoxy]-2-fluorophenyl]-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C(C(=C1)F)=CC=C1OCC1C(Cl)(Cl)C1 SUKKLVJALGDLLT-UHFFFAOYSA-N 0.000 description 1
- MRJOGDDJPVLGIY-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-[(4-chlorophenyl)methoxy]phenyl]-1-ethoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound C=1C=C(OCC=2C=CC(Cl)=CC=2)C=CC=1C(=NOCC)C(C)=NOCC1=CC=CC=C1C(=COC)C(=O)OC MRJOGDDJPVLGIY-UHFFFAOYSA-N 0.000 description 1
- MAFSBIFLPHWKFC-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-[2-(2,4-dichlorophenyl)ethyl]phenyl]-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C(C=C1)=CC=C1CCC1=CC=C(Cl)C=C1Cl MAFSBIFLPHWKFC-UHFFFAOYSA-N 0.000 description 1
- UVUDXSCTHDVTMD-UHFFFAOYSA-N methyl 2-[2-[[[1-[4-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]phenyl]-1-methoxyiminopropan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C(C=C1)=CC=C1CCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UVUDXSCTHDVTMD-UHFFFAOYSA-N 0.000 description 1
- KYAPFMGPPGNNJF-UHFFFAOYSA-N methyl 2-[2-[[[1-butoxyimino-1-[4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]propan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C(F)(F)F)C=CC=1C(=NOCCCC)C(C)=NOCC1=CC=CC=C1C(=COC)C(=O)OC KYAPFMGPPGNNJF-UHFFFAOYSA-N 0.000 description 1
- QBSUATFQLKIVIV-UHFFFAOYSA-N methyl 2-[2-[[[1-ethoxyimino-1-[4-[(4-fluorophenyl)methoxy]phenyl]propan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound C=1C=C(OCC=2C=CC(F)=CC=2)C=CC=1C(=NOCC)C(C)=NOCC1=CC=CC=C1C(=COC)C(=O)OC QBSUATFQLKIVIV-UHFFFAOYSA-N 0.000 description 1
- JWNFQXDQDMQFSH-UHFFFAOYSA-N methyl 2-[2-[[[1-ethoxyimino-1-[4-[3-(trifluoromethyl)phenoxy]phenyl]propan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound CCON=C(C(C)=NOCC1=C(C=CC=C1)C(=COC)C(=O)OC)C1=CC=C(OC2=CC(=CC=C2)C(F)(F)F)C=C1 JWNFQXDQDMQFSH-UHFFFAOYSA-N 0.000 description 1
- BSHPQGKUYJYTMR-UHFFFAOYSA-N methyl 2-[2-[[[1-ethoxyimino-1-[4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]propan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound CCON=C(C(C)=NOCC1=C(C=CC=C1)C(=COC)C(=O)OC)C1=CC=C(OCC2=CC(=CC=C2)C(F)(F)F)C=C1 BSHPQGKUYJYTMR-UHFFFAOYSA-N 0.000 description 1
- HZQIEJUSDDZAPZ-UHFFFAOYSA-N methyl 2-[2-[[[1-ethoxyimino-1-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]propan-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound C=1C=C(OCC=2C=CC(=CC=2)C(F)(F)F)C=CC=1C(=NOCC)C(C)=NOCC1=CC=CC=C1C(=COC)C(=O)OC HZQIEJUSDDZAPZ-UHFFFAOYSA-N 0.000 description 1
- SKUXXXACWOSDCT-UHFFFAOYSA-N methyl 2-methoxyimino-2-[2-[[[1-methoxyimino-1-(2-methyl-4-propoxyphenyl)propan-2-ylidene]amino]oxymethyl]phenyl]acetate Chemical compound CC1=CC(OCCC)=CC=C1C(=NOC)C(C)=NOCC1=CC=CC=C1C(=NOC)C(=O)OC SKUXXXACWOSDCT-UHFFFAOYSA-N 0.000 description 1
- UTMOBULVJAMMLX-UHFFFAOYSA-N methyl 2-methoxyimino-2-[2-[[[1-methoxyimino-1-(4-propoxyphenyl)propan-2-ylidene]amino]oxymethyl]phenyl]acetate Chemical compound C1=CC(OCCC)=CC=C1C(=NOC)C(C)=NOCC1=CC=CC=C1C(=NOC)C(=O)OC UTMOBULVJAMMLX-UHFFFAOYSA-N 0.000 description 1
- ZIWSIOHGOKCNPS-UHFFFAOYSA-N methyl 2-methoxyimino-2-[2-[[[1-methoxyimino-1-[4-[3-(trifluoromethyl)phenoxy]phenyl]propan-2-ylidene]amino]oxymethyl]phenyl]acetate Chemical compound C=1C=C(OC=2C=C(C=CC=2)C(F)(F)F)C=CC=1C(=NOC)C(C)=NOCC1=CC=CC=C1C(=NOC)C(=O)OC ZIWSIOHGOKCNPS-UHFFFAOYSA-N 0.000 description 1
- LFYGWTBWUMZXDD-UHFFFAOYSA-N methyl 3-methoxy-2-[2-[[[1-methoxyimino-1-[4-(2-methylpropoxy)phenyl]propan-2-ylidene]amino]oxymethyl]phenyl]prop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C1=CC=C(OCC(C)C)C=C1 LFYGWTBWUMZXDD-UHFFFAOYSA-N 0.000 description 1
- IQQNFJGPCUJGBV-UHFFFAOYSA-N methyl 3-methoxy-2-[2-[[[1-methoxyimino-1-[4-[2-[3-(trifluoromethyl)phenyl]ethyl]phenyl]propan-2-ylidene]amino]oxymethyl]phenyl]prop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOC)C(C=C1)=CC=C1CCC1=CC=CC(C(F)(F)F)=C1 IQQNFJGPCUJGBV-UHFFFAOYSA-N 0.000 description 1
- OLBZASKPJFTFRJ-UHFFFAOYSA-N methyl 3-methoxy-2-[2-[[[1-methoxyimino-1-[4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]butan-2-ylidene]amino]oxymethyl]phenyl]prop-2-enoate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C(F)(F)F)C=CC=1C(=NOC)C(CC)=NOCC1=CC=CC=C1C(=COC)C(=O)OC OLBZASKPJFTFRJ-UHFFFAOYSA-N 0.000 description 1
- HWOVSFZPVNJHCQ-UHFFFAOYSA-N methyl 3-methoxy-2-[2-[[[1-prop-2-ynoxyimino-1-[4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]propan-2-ylidene]amino]oxymethyl]phenyl]prop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CON=C(C)C(=NOCC#C)C(C=C1)=CC=C1OCC1=CC=CC(C(F)(F)F)=C1 HWOVSFZPVNJHCQ-UHFFFAOYSA-N 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
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- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229910052707 ruthenium Inorganic materials 0.000 description 1
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- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
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- 150000003455 sulfinic acids Chemical class 0.000 description 1
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- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- JTCWXISSLCZBQV-UHFFFAOYSA-N tribol Natural products CC(CO)CCC1OC2(O)CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C2C1C)OC6OC(CO)C(OC7OC(C)C(O)C(O)C7O)C(O)C6OC8OC(C)C(O)C(O)C8O JTCWXISSLCZBQV-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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- A—HUMAN NECESSITIES
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- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
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- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
- C07C255/64—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/47—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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CH346595 | 1995-12-07 | ||
CH346495 | 1995-12-07 | ||
CH122696 | 1996-05-14 | ||
CH168896 | 1996-07-05 | ||
CH249396 | 1996-10-11 | ||
PCT/EP1996/005226 WO1997020809A1 (fr) | 1995-12-07 | 1996-11-25 | Pesticides |
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Publication Number | Publication Date |
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EA199800507A1 EA199800507A1 (ru) | 1999-02-25 |
EA001313B1 true EA001313B1 (ru) | 2001-02-26 |
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EA199800507A EA001313B1 (ru) | 1995-12-07 | 1996-11-25 | Пестициды |
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US (2) | US5985921A (fr) |
EP (2) | EP0865424B1 (fr) |
JP (1) | JP2000501401A (fr) |
KR (1) | KR19990071934A (fr) |
CN (2) | CN1238337C (fr) |
AT (1) | ATE224361T1 (fr) |
AU (1) | AU723372B2 (fr) |
BR (1) | BR9611811A (fr) |
CA (1) | CA2238632A1 (fr) |
CO (1) | CO4750752A1 (fr) |
CZ (1) | CZ173298A3 (fr) |
DE (1) | DE69623806T2 (fr) |
DK (1) | DK0865424T3 (fr) |
EA (1) | EA001313B1 (fr) |
ES (1) | ES2183985T3 (fr) |
HU (1) | HUP9900091A3 (fr) |
IL (1) | IL124523A (fr) |
MA (1) | MA24028A1 (fr) |
NZ (1) | NZ323666A (fr) |
PL (1) | PL185913B1 (fr) |
PT (1) | PT865424E (fr) |
TR (1) | TR199801045T2 (fr) |
WO (1) | WO1997020809A1 (fr) |
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Publication number | Priority date | Publication date | Assignee | Title |
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HUP9900736A2 (hu) * | 1995-10-18 | 1999-06-28 | Bayer Ag. | Fluor-metoxi-akrilsav-származékok és kártevőirtó szerként történő alkalmazásuk |
DE19711168A1 (de) * | 1997-03-18 | 1998-09-24 | Basf Ag | Phenylketiminooxybenzylverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
AR015821A1 (es) * | 1997-05-27 | 2001-05-30 | Bayer Ag | Compuestos organicos |
EP0984923A1 (fr) * | 1997-05-27 | 2000-03-15 | Novartis AG | O-benzyle oxime ethers et utilisation de ces composes comme pesticides |
AUPO715897A0 (en) | 1997-06-03 | 1997-06-26 | O'dwyer, James Michael | Firearms |
GB9718366D0 (en) * | 1997-08-29 | 1997-11-05 | Ciba Geigy Ag | Novel combinations |
US6313344B1 (en) | 1998-05-27 | 2001-11-06 | Bayer Aktiengesellschaft | Organic compounds |
GB9820582D0 (en) * | 1998-09-22 | 1998-11-11 | Novartis Ag | Organic compounds |
US6525092B1 (en) | 1998-09-22 | 2003-02-25 | Bayer Aktiengsellschaft | Pesticidal bis-oxime compounds |
JP2003516384A (ja) * | 1999-12-06 | 2003-05-13 | バイエル アクチェンゲゼルシャフト | 殺微生物剤、殺虫剤及び殺ダニ剤効果を有するn−フェニルカルバメート |
DE10101150A1 (de) | 2001-01-12 | 2002-07-18 | Bayer Ag | Verfahren zur Herstellung trifluormethyl-substituierter Biphenylcarbonsäuren und neue trichlormethyl-und trifluormethyl-substituierte Biphenylcarbonitrile |
DE10209145A1 (de) * | 2002-03-01 | 2003-09-04 | Bayer Cropscience Ag | Halogenbenzole |
DE102006016641A1 (de) * | 2006-04-08 | 2007-10-11 | Bayer Cropscience Ag | Verwendung von 3-(2,4,6-Trimethylphenyl)-4-neopentylcarbonyloxy-5,5-tetramethylen-Δ3-dihydrofuran-2-on zur Bekämpfung von Dipteren aus der Familie der Cecidomyiidae |
CN104429735A (zh) * | 2014-11-12 | 2015-03-25 | 浙江省农业科学院 | 含有食用油和有机硅混合的农药试剂以及用途 |
EP3047731A1 (fr) | 2015-01-21 | 2016-07-27 | Basf Se | Procédé de lutte contre la rouille du soja comprenant le traitement du soja avec des (2E)-2-[3-substitués-2 [[(E)-[(2E)-2-alkoxyimino-1-méthyl-2-phényl-ethylidene]amino]oxyméthyl]phényl]-2-méthoxy-imino-N-méthyl-acétamides |
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EP0370629B2 (fr) * | 1988-11-21 | 1998-01-07 | Zeneca Limited | Fongicides |
HU216144B (hu) * | 1988-12-29 | 1999-04-28 | Novartis Ag. | Hatóanyagként akrilsavszármazékot tartalmazó fungicid készítmény, és eljárás a hatóanyag előállítására |
US5104872A (en) * | 1989-08-22 | 1992-04-14 | Nihon Hohyaku Co., Ltd. | N-(substituted benzyloxy) imine derivatives and method of use thereof |
PH11991042549B1 (fr) * | 1990-06-05 | 2000-12-04 | ||
DE59109047D1 (de) * | 1990-06-27 | 1998-10-08 | Basf Ag | O-Benzyl-Oximether und diese Verbindungen enthaltende Pflanzenschutzmittel |
GB9018408D0 (en) * | 1990-08-22 | 1990-10-03 | Ici Plc | Fungicides |
WO1992013830A1 (fr) * | 1991-01-30 | 1992-08-20 | Zeneca Limited | Fongicides |
NZ242290A (en) * | 1991-04-15 | 1994-12-22 | Zeneca Ltd | Pyridyl and pyrimidinyl substituted oxime-o-benzyl ether derivatives; preparatory processes, fungicidal compositions and an intermediate |
CH686307A5 (de) * | 1991-04-19 | 1996-02-29 | Ciba Geigy Ag | Oximether des 3-Methoxy-2-(o-tolyl)acrylsouremethylesters, Verfahren zu ihrer Herstellung und fungizide Mittel, die diese als Wirkstoffe enthalten. |
HU219157B (hu) * | 1994-01-05 | 2001-02-28 | Novartis Ag. | Peszticid hatású [dioxa-diaza/vagy oxa-triaza/-heptadienil-fenil]-akrilsav- és glioxilsav-származékok, előállításuk és alkalmazásuk |
NZ278072A (en) * | 1994-02-04 | 1998-02-26 | Basf Ag | Phenylacetic acid oxime derivatives; biocides |
RU2165411C2 (ru) * | 1994-02-04 | 2001-04-20 | Басф Акциенгезельшафт | Производные фенилуксусной кислоты, промежуточные продукты для их получения и содержащие их средства |
MX9603175A (es) * | 1994-02-04 | 1997-04-30 | Basf Ag | Derivados de acido fenilacetico, preparaciones de los mismos e intermediarios para los mismos, y composiciones que los contienen. |
DK0765304T4 (da) | 1994-06-10 | 2007-12-03 | Bayer Cropscience Ag | Fremgangsmåde og mellemprodukter til fremstilling af a-methoxyiminocarboxylsyremethylamider |
CH689228A5 (de) * | 1994-10-07 | 1998-12-31 | Novartis Ag | Oximether, sowie diese enthaltende Pflanzenschutzmittel. |
SK61397A3 (en) * | 1994-11-17 | 1997-11-05 | Ciba Geigy Ag | O-benzyl oxime ether derivatives, intermediate products, pesticides containing the same and their use |
NZ307197A (en) * | 1995-05-09 | 1999-03-29 | Basf Ag | (het)aryloxy-, -thio-, aminocrotonates and their use as insecticides and fungicides |
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1996
- 1996-11-25 PT PT96940650T patent/PT865424E/pt unknown
- 1996-11-25 CN CNB021504423A patent/CN1238337C/zh not_active Expired - Fee Related
- 1996-11-25 KR KR1019980704221A patent/KR19990071934A/ko not_active Application Discontinuation
- 1996-11-25 TR TR1998/01045T patent/TR199801045T2/xx unknown
- 1996-11-25 CN CN96199572A patent/CN1117071C/zh not_active Expired - Fee Related
- 1996-11-25 NZ NZ323666A patent/NZ323666A/xx unknown
- 1996-11-25 CA CA002238632A patent/CA2238632A1/fr not_active Abandoned
- 1996-11-25 JP JP9520940A patent/JP2000501401A/ja active Pending
- 1996-11-25 DE DE69623806T patent/DE69623806T2/de not_active Expired - Lifetime
- 1996-11-25 WO PCT/EP1996/005226 patent/WO1997020809A1/fr not_active Application Discontinuation
- 1996-11-25 ES ES96940650T patent/ES2183985T3/es not_active Expired - Lifetime
- 1996-11-25 EA EA199800507A patent/EA001313B1/ru not_active IP Right Cessation
- 1996-11-25 DK DK96940650T patent/DK0865424T3/da active
- 1996-11-25 EP EP96940650A patent/EP0865424B1/fr not_active Expired - Lifetime
- 1996-11-25 PL PL96327162A patent/PL185913B1/pl unknown
- 1996-11-25 AT AT96940650T patent/ATE224361T1/de not_active IP Right Cessation
- 1996-11-25 EP EP02002070A patent/EP1207152A3/fr not_active Withdrawn
- 1996-11-25 BR BR9611811A patent/BR9611811A/pt unknown
- 1996-11-25 AU AU10662/97A patent/AU723372B2/en not_active Ceased
- 1996-11-25 IL IL12452396A patent/IL124523A/xx not_active IP Right Cessation
- 1996-11-25 HU HU9900091A patent/HUP9900091A3/hu unknown
- 1996-11-25 CZ CZ981732A patent/CZ173298A3/cs unknown
- 1996-12-04 CO CO96063584A patent/CO4750752A1/es unknown
- 1996-12-05 MA MA24417A patent/MA24028A1/fr unknown
- 1996-12-06 US US08/761,675 patent/US5985921A/en not_active Expired - Lifetime
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1999
- 1999-06-29 US US09/343,662 patent/US6420423B1/en not_active Expired - Fee Related
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